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Product Details of [ 576-83-0 ]

CAS No. :576-83-0 MDL No. :MFCD00000073
Formula : C9H11Br Boiling Point : -
Linear Structure Formula :- InChI Key :RRTLQRYOJOSPEA-UHFFFAOYSA-N
M.W : 199.09 Pubchem ID :68473
Synonyms :

Calculated chemistry of [ 576-83-0 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.04
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.63
Log Po/w (XLOGP3) : 3.71
Log Po/w (WLOGP) : 3.37
Log Po/w (MLOGP) : 3.98
Log Po/w (SILICOS-IT) : 3.9
Consensus Log Po/w : 3.52

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.86
Solubility : 0.0278 mg/ml ; 0.000139 mol/l
Class : Soluble
Log S (Ali) : -3.4
Solubility : 0.0791 mg/ml ; 0.000397 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.42
Solubility : 0.00766 mg/ml ; 0.0000385 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.15

Safety of [ 576-83-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 576-83-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 576-83-0 ]
  • Downstream synthetic route of [ 576-83-0 ]

[ 576-83-0 ] Synthesis Path-Upstream   1~33

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Reference: [1] Patent: US5554620, 1996, A,
  • 2
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  • [ 773-64-8 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 12, p. 3170 - 3173
  • 3
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  • [ 27129-86-8 ]
  • [ 576-83-0 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
[2] Journal of Organometallic Chemistry, 2005, vol. 690, # 4, p. 1067 - 1079
[3] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3247 - 3250
  • 4
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YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide In 1,2-dichloro-ethane at 25℃; for 12 h; Sealed tube General procedure: NBS (1.0 mmol) and catalyst 1 (0.1 or 1 mol percent Au based on the substrate) were weighted into a 10 mL sealed vessel, and then DCE (2 mL) and the substrate (1.0 mmol) were added. The reaction was stirred at the required temperature for the specified time. After reaction, the catalyst was removed with a magnet, and the solution was concentrated under reduced pressure and purified by column chromatography.
95 %Chromat. With carbon dioxide; oxygen; lithium bromide; copper(ll) bromide In water at 100℃; for 10 h; Autoclave; Green chemistry General procedure: A mixture of substrate (1 mmol), CuBr2 (22.4 mg, 10 molpercent), LiBr (130.3 mg, 1.5 equiv.), and 0.05 mL of water was placed in a 50 mL stainless steel autoclave equipped with an inner glass tube in room temperature. CO2 (4 MPa) and O2 (1 MPa) were subsequently introduced into the autoclave and the system was heated under the predetermined reaction temperature for 15 min to reach the equilibration. Then the final pressure was adjusted to the desired pressure by introducing the appropriate amount of CO2. The mixture was stirred continuously for the desired reaction time. After cooling, products were diluted with acetone and analyzed by gas chromatograph (Shimadzu GC-2014) equipped with a capillary column (RTX-17 30 m × 25 μm and RTX-wax 30 m × 25 μm) using a flame ionization detector by comparing the retention times of authentic samples. The residue was purified by column chromatography on silica gel (200–300 mesh, eluting with petroleum ether/ethyl acetate from petroleum ether to 50:1) to afford the desired product. The isolated products were further identified with NMR spectra (Bruker 400 MHz) and GC–MS or GCD, which are consistent with those reported in the literature.
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 11, p. 3072 - 3075
[2] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
[3] Angewandte Chemie - International Edition, 2010, vol. 49, # 11, p. 2028 - 2032
[4] Tetrahedron Letters, 2013, vol. 54, # 9, p. 1063 - 1066
[5] Synthesis, 2002, # 2, p. 169 - 171
[6] Tetrahedron Letters, 2003, vol. 44, # 49, p. 8781 - 8785
[7] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938
[8] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 439 - 443
[9] Canadian Journal of Chemistry, 2009, vol. 87, # 2, p. 440 - 447
[10] Organic Preparations and Procedures International, 1997, vol. 29, # 6, p. 715 - 719
[11] Helvetica Chimica Acta, 2003, vol. 86, # 1, p. 164 - 168
[12] Synthetic Communications, 2004, vol. 34, # 12, p. 2143 - 2152
[13] Angewandte Chemie - International Edition, 2018, vol. 57, # 39, p. 12869 - 12873[14] Angew. Chem., 2018, vol. 130, p. 13051 - 13055,5
[15] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 11, p. 4149 - 4150
[16] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 11, p. 4149 - 4150
[17] Tetrahedron Letters, 2006, vol. 47, # 7, p. 1097 - 1099
[18] Synthesis, 2011, # 2, p. 207 - 209
[19] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[20] Journal of Organic Chemistry, 2004, vol. 69, # 14, p. 4663 - 4669
[21] Journal of Organic Chemistry, 1992, vol. 57, # 9, p. 2740 - 2741
[22] European Journal of Organic Chemistry, 2006, # 2, p. 483 - 488
[23] Organic Letters, 2013, vol. 15, # 9, p. 2108 - 2111
[24] Tetrahedron, 1997, vol. 53, # 7, p. 2581 - 2584
[25] Bulletin de la Societe Chimique de France, 1981, vol. 1, # 1-2, p. 42 - 48
[26] Journal of the Indian Chemical Society, 1936, vol. 13, p. 192
[27] Journal of the American Chemical Society, 1956, vol. 78, p. 4549,4552
[28] Justus Liebigs Annalen der Chemie, 1868, vol. 147, p. 8
[29] Chemische Berichte, 1886, vol. 19, p. 213
[30] Patent: DE123746, , ,
[31] Journal fuer Praktische Chemie (Leipzig), 1929, vol. <2> 124, p. 132
[32] Journal of the American Chemical Society, 1929, vol. 51, p. 3002
[33] Organic Syntheses, 1931, vol. 11, p. 24
[34] Journal of the American Chemical Society, 1916, vol. 38, p. 2548
[35] Liebigs Annalen der Chemie, 1981, # 7, p. 1190 - 1197
[36] Synthesis, 1993, # 2, p. 237 - 241
[37] Tetrahedron Letters, 1994, vol. 35, # 18, p. 2841 - 2844
[38] Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 236 - 237
[39] Synthetic Communications, 2000, vol. 30, # 12, p. 2091 - 2098
[40] Bulletin of the Chemical Society of Japan, 2002, vol. 75, # 2, p. 339 - 345
[41] Tetrahedron, 2005, vol. 61, # 49, p. 11657 - 11663
[42] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3247 - 3250
[43] Synlett, 2006, # 18, p. 3176 - 3178
[44] Synthesis, 2010, # 10, p. 1629 - 1632
[45] Patent: EP2216312, 2010, A1, . Location in patent: Page/Page column 78
[46] Journal of Chemical Research, 2012, vol. 36, # 5, p. 258 - 260
[47] Green Chemistry, 2012, vol. 14, # 6, p. 1673 - 1679
[48] Synthesis (Germany), 2013, vol. 45, # 11, p. 1497 - 1504
[49] Organic Process Research and Development, 2004, vol. 8, # 4, p. 568 - 570
[50] Catalysis Today, 2012, vol. 194, # 1, p. 38 - 43
[51] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2800 - 2807
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YieldReaction ConditionsOperation in experiment
73% With bromine In tetrachloromethane Example 1; Bromination of Mesitylene Using Elemental Bromine:; The bromination of mesitylene (1) using elemental bromine was carried out in a static micromixer (Technical University of Ilmenau, Faculty of Machine Construction, Dr. -Ing. Norbert Schwesinger, P.O. Box 100565, D-98684, Ilmenau) having a physical size of 0.8 mm.x.0.8 mm.x.0.6 mm and a total volume of 0.125 μl and a total pressure loss of about 1000 Pa. The static micromixer was connected to a Teflon capillary having an internal diameter of 0.25 mm and a length of 1 m via an outlet and an Omnifit medium-pressure HPLC connector (Omnifit, Germany). The temperatures of the static micro-mixer and the Teflon capillary were regulated in an water-filled jacketed vessel thermostatted to 10° C.In order to prepare a solution of mesitylene, 1.2 g (0.01 mol) of mesitylene were diluted with tetrachloromethane to a total volume of 2 ml. In order to prepare a solution of elemental bromine, 1.7 g (0.011 mol) of bromine were diluted with tetrachloromethane to a total volume of 2 ml. The two solutions were subsequently transferred into the static micromixer using a metering pump (Harvard Apparatus Inc., Pump 22, South Natick, Mass., USA) and 2 ml polypropylene syringes (B. Braun Melsungen AG, Germany). The flow rate here was set to 10 ml/min. The mixed reaction solution was subsequently passed into 2 ml of an HPLC buffer solution comprising acetonitrile and 1percent trifluoroacetic acid in the ratio 1:1 (Merck, Darmstadt) in order to terminate the bromination reaction. The reaction mixture was evaluated by combined GC/MS analysis. The reaction mixture comprised 88 area-percent of the chromatogram of the monobrominated product (2), 9 area-percent of the dibrominated product (3) and 3 area-percent of the unbrominated mesitylene (1).In order to determine the preparative yield of the brominated reaction products, the mixed reaction solution was stirred into a beaker containing 50 ml of water. The system comprising static micromixer and Teflon capillary was subsequently rinsed firstly with 10 ml of water and subsequently with 10 ml of dichloromethane. The combined liquid phases were then stirred for 20 minutes and subsequently extracted three times with 20 ml of diethyl ether each time. The combined ethereal extracts were dried over magnesium sulfate and freed from solvent under reduced pressure, giving 1.7 g (corresponding to 73percent of the theoretical yield) of a brownish oil, whose content of monobrominated product (2) was determined by combined GC/MS analysis as 85 area-percent of the chromatogram.; Example 2; The set-up and performance were as in Example 1, but the flow rate was set to 20 μl/min. Combined GC/MS analysis of the reaction mixture obtained in this way gave a composition of 51 area-percent of the chromatogram of the mono-brominated product (2), 47 area-percent of the dibrominated product (3) and 2 area-percent of mesitylene brominated in the methyl side chain.
Reference: [1] Patent: US7271302, 2007, B1, . Location in patent: Page/Page column 5-6
[2] Bulletin of the Chemical Society of Japan, 2001, vol. 74, # 6, p. 1151 - 1152
[3] Organic Preparations and Procedures International, 1995, vol. 27, # 6, p. 652 - 656
[4] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 2093 - 2094
[5] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 2093 - 2094
[6] Green Chemistry, 2012, vol. 14, # 6, p. 1673 - 1679
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Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
[2] Journal of Organometallic Chemistry, 2005, vol. 690, # 4, p. 1067 - 1079
[3] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3247 - 3250
  • 7
  • [ 88-05-1 ]
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 55, p. 14622 - 14626
[2] Journal of Organic Chemistry, 1977, vol. 42, p. 2426 - 2431
  • 8
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Reference: [1] Chemical Science, 2018, vol. 9, # 15, p. 3860 - 3865
  • 9
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  • [ 60057-49-0 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 500 - 511
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Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1982, vol. 31, # 2, p. 350 - 357[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 2, p. 387 - 395
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  • [ 1667-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 2, p. 445 - 452
[2] Chinese Chemical Letters, 2011, vol. 22, # 2, p. 147 - 150
  • 12
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  • [ 1332484-20-4 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 19, p. 4988 - 4991
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  • [ 108-67-8 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 13, p. 4290 - 4293
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Reference: [1] Green Chemistry, 2012, vol. 14, # 6, p. 1673 - 1679
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Reference: [1] Journal of the Indian Chemical Society, 1939, vol. 16, p. 460
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  • [ 108-67-8 ]
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Reference: [1] Journal of the Indian Chemical Society, 1936, vol. 13, p. 192
[2] Journal of the American Chemical Society, 1916, vol. 38, p. 2548
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  • [ 608-72-0 ]
Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1,9
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  • [ 6942-99-0 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 6, p. 1673 - 1679
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Reference: [1] Journal of the American Chemical Society, 1936, vol. 58, p. 1,9
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  • [ 576-83-0 ]
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Reference: [1] Journal of the American Chemical Society, 1942, vol. 64, p. 2888,2890
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YieldReaction ConditionsOperation in experiment
58%
Stage #1: With magnesium In tetrahydrofuran for 4.5 h; Heating / reflux
Stage #2: With triethyl borate In tetrahydrofuran at -78 - 20℃; for 5.25 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 2 h;
Magnesium (60.27 mmol) and tetrahydrofuran (30 mL) were put in a three-necked round bottom flask and stirred. To the solution, bromomesitylene (13.07 mmol) was added, and the reaction mixture was heated. After that, bromomesitylene (32.02 mmol) dissolved in tetrahydrofuran (30 mL) was added dropwise to the solution. The reaction mixture was heated and refluxed for 4.5 hours. Then, the mixture was cooled to -78°C. (EtO)3B (111.66 mmol) was added dropwise over 15 minutes. After that, the mixture was warmed to room temperature and stirred for additional 5 hours. Then the mixture was cooled to 0°C. The reaction was quenched by the addition of 1 M hydrochloric acid and stirring for additional 2 hours. The reaction mixture was extracted with diethyl ether three times. The combined extracts was washed with brine and dried over anhydrous sodium sulfate. After the drying, the extract was filtered. The filtrate was concentrated to give a solid, which was recrystallized in benzene to give GA33 (26.10 mmol, yield: 58percent). 1H-NMR(400MHz,CDCl3) δ = 6.82(s,2H), 4.73(brs,2H), 2.33(s,6H), 2.26(s,3H). 13C-NMR(100MHz,CDCl3) δ = 139.64, 138.66, 127.99, 127.26, 22.89, 22.03, 21.12.
Reference: [1] Organic Letters, 2011, vol. 13, # 17, p. 4479 - 4481
[2] Patent: EP1623971, 2006, A1, . Location in patent: Page/Page column 19
[3] Journal of Organic Chemistry, 2000, vol. 65, # 20, p. 6319 - 6337
[4] Organic Letters, 2014, vol. 16, # 17, p. 4662 - 4665
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YieldReaction ConditionsOperation in experiment
85%
Stage #1: With magnesium In tetrahydrofuran for 3 h; Reflux
Stage #2: at -78 - 20℃; for 12 h;
General procedure: A solution of 1 equiv. (10 mmol) mesitylbromide and 5 ml THF was addeddropwise to 1.2 equiv. (12 mmol, 0.30g) activated Mg turnings in 10 ml THF.After the reaction started, the mixture was refluxed for 3 hours. Then the reactionmixture was cooled to -78°C, and treated with 2 equiv. (20 mmol, 2.0g) offreshly distilled trimethylborate, and then the reaction mixture was allowed to warm up toroom temperature, and stirred overnight (12 hours). The reaction was quenched with 2 equiv.(20 mmol, 20 ml) 1M HCl-solution at 0 °C, then the mixture was stirred at rt. for two hours.The phases were separated and the aqueous phase was washed with 3x10 ml diethyl ether.The combined organic layer was washed with brine three times, dried over anhydrousNa2SO4, filtered off and evaporated to dryness. The resulted solid/oil was suspended in hexane,filtered off, washed with hexane 3 times and dried.
Reference: [1] Journal of Organometallic Chemistry, 2017, vol. 847, p. 258 - 262
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Reference: [1] New Journal of Chemistry, 2002, vol. 26, # 4, p. 373 - 375
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Reference: [1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2800 - 2807
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Reference: [1] New Journal of Chemistry, 2002, vol. 26, # 4, p. 373 - 375
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YieldReaction ConditionsOperation in experiment
79%
Stage #1: With magnesium In tetrahydrofuran for 3 h; Inert atmosphere; Cooling with ice; Reflux
Stage #2: at 0 - 20℃; for 12 h; Inert atmosphere
In a 100 ml, two-necked, round-bottomedflask flushed with nitrogen and provided with a reflux condenser whose top was connected toa nitrogen inlet were placed 1.07 g (44 mmol) of magnesium turnings and 7.96 g (40 mmol)2-bromomesitylene. With stirring and ice bath at hand, 14 ml of anhydrous THF was added inone portion. The mixture had to be warmed to initiate reaction, but the ice bath was necessaryto control frothing once the exotherm had begun. After heat evolution had subsided, another 20 ml of anhydrous THF was added, and the mixture was heated under reflux for another 3hours. The reaction mixture was allowed to cool to room temperature.The Grignard reagent was added dropwise by syringe to a solution of BF3*OEt2 (2.3 ml, 18.4mmol) in 20 mL of anhydrous THF at 0°C. After that, the reaction mixture was allowed towarm up to room temperature, and stirred overnight (12 hours). The solvent was evaporatedand the residue was extracted with hexane (80 ml). The resulting suspension was filtered usinga Schlenk filter and the supernatant was concentrated under reduced pressure. The crudeproduct was purified by sublimation in vacuo, at 110°C/ 0.05 mmHg. The product was whitesolid. Yield: 3.9 g (79percent). 1H NMR (300 MHz, CDCl3) 2.30 (s, 6H), 2.31 (s, 6H), 2.34 (s,6H), 6.87 (s, 4H). 13C NMR (75 MHz, CDCl3) 21.3, 22.3, 128.5 (CH), 140.6, 142.4. 11BNMR (160 MHz, CDCl3) 53.2. 19F NMR (282 MHz, CDCl3) -14.62. HRMS (ESI) calcd.for C18H22BF [M-F]+, 249.1815, found: 249.1815
78%
Stage #1: With magnesium In tetrahydrofuran for 2 h; Reflux
Stage #2: at 0℃; for 2 h; Reflux
Weigh the Mg strip (200 mmol) into a 250 mL three-necked flask.While stirring, the gas was quickly and repeatedly degassed and replaced with nitrogen.S23 (200 mmol) and dry tetrahydrofuran (100 mL) were added, and the reaction was initiated by heating, and the reaction was carried out under reflux for 2 h.The reaction mixture was cooled to 0 ° C, and boron trifluoride diethyl ether solution (90 mmol) was added dropwise at 0 ° C.The reaction was refluxed again for 2 h to obtain a suspension of S24 in THF.The solvent was distilled off under reduced pressure, and purified by column chromatography, using hexane as eluent, and solvent was removed to give S24 (156 mmol, 78percent).
Reference: [1] Synlett, 2014, vol. 25, # 11, p. 1525 - 1528
[2] Patent: CN108586441, 2018, A, . Location in patent: Paragraph 0200-0201
[3] Journal of Materials Chemistry C, 2016, vol. 4, # 20, p. 4393 - 4401
[4] Organometallics, 2018, vol. 37, # 19, p. 3360 - 3367
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YieldReaction ConditionsOperation in experiment
78%
Stage #1: With magnesium In tetrahydrofuran for 2 h; Inert atmosphere; Reflux
Stage #2: at 0℃; for 2 h; Reflux
Weigh the Mg strip (200 mmol) into a 250 mL three-necked flask.While stirring, 3 times of degassing and nitrogen replacement were quickly repeated.Add S9 (200 mmol) and dry tetrahydrofuran (100 mL).The reaction was initiated by heating and reacted under reflux for 2 h.The reaction mixture was cooled to 0 ° C.Add boron trifluoride diethyl ether solution (90 mmol) dropwise at 0 °C.The reaction was refluxed again for 2 h to obtain a suspension of S10 in THF.The solvent was distilled off under reduced pressure and purified by column chromatography.Using n-hexane as the eluent,Remove solvent to get S24(156 mmol, 78percent).
Reference: [1] Patent: CN108727405, 2018, A, . Location in patent: Paragraph 0132; 0133; 0134
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Reference: [1] Patent: CN107417571, 2017, A,
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Reference: [1] Chemische Berichte, 1894, vol. 27, p. 3444[2] Chemische Berichte, 1895, vol. 28, p. 531
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YieldReaction ConditionsOperation in experiment
61%
Stage #1: at -78℃; for 1 h;
Stage #2: at -78 - 23℃; for 4 h;
TERT-BUTYLLITHIUM (90.6 mL, 154 mmol; 1.7 M in pentane) was added via cannula to a stirred solution of tetrahydrofuran (380 mL) under an atmosphere of nitrogen at room temperature. The reaction mixture was cooled to-78°C before adding 2-bromomesitylene (11.3 mL, 74.1 mmol) dropwise. The reaction mixture was allowed to stir for 1 hour at- 78°C. To the reaction mixture at-78°C was added 4-methoxypyridine (5.79 ML, 57 mmol) dropwise, and the resulting mixture was stirred AT-23°C for 3 hours. The reaction mixture was then re-cooled to-78°C and DIMETHYLFORMAMIDE (6.62 mL, 85.5 mmol) was added and stirring was continued for 1 hour AT-78°C. The reaction mixture was quenched slowly AT-78°C with saturated aqueous sodium chloride solution (100 mL) and allowed to warm to room temperature slowly. To the reaction mixture was added diethyl ether (200 mL) and the layers were separated. The aqueous layer was extracted with diethyl ether (2 x 150 mL) and the combined organic layers were dried over potassium carbonate (20 g). The potassium carbonate was removed by filtration and washed with diethyl ether (100 mL) and the solvent removed under reduced pressure. The resulting crude 4-methoxy-3- pyridinecarboxaldehyde was purified by column chromatography (SiO2, 5: 95 ethanol: ethyl acetate) to give 4.79 g of the title intermediate as a yellow solid (61percent yield; >98percent purity by'H NMR). Analytical Data : HNMR (300 MHz, CDCL) 8 10.43 (s, 1H, CHO), 8.87 (s, 1H, ArH), 8.63 (d, 1H, J= 6, ARH), 6.92 (d, 1H, J= 6, ART), 3.98 (s, 3H, CH30).
Reference: [1] Patent: WO2004/41806, 2004, A2, . Location in patent: Page 65
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Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7729 - 7737
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  • [ 576-83-0 ]
  • [ 134030-21-0 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 23, p. 7729 - 7737
  • 33
  • [ 576-83-0 ]
  • [ 27006-02-6 ]
  • [ 400822-47-1 ]
YieldReaction ConditionsOperation in experiment
10% With lead dioxide; trifluoroacetic acid In dichloromethane at 20℃; for 40 h; General procedure: Compound 1a, 1b, 3a, 3b, 7a, or 7b, 0.57 mmol, was added with vigorous stirring at 20°C to a solution of 0.2 mL (2.6 mmol) of trifluoroacetic acid in 3 mL of methylene chloride, 136 mg (0.57 mmol) of lead(IV) oxide was then added, and the mixture was stirred for 2–70 h. When the reaction was complete, the mixture was treated with water (50 mL) and extracted with chloroform (3 ×50 mL). The combined extracts were washed with water, a saturated aqueous solution of NaHCO3, and water again and dried over Na2SO4, and the solvent was distilled off. The residue was subjected to silica gel column chromatography using petroleum ether–ethyl acetate as eluent. Given below are the yields of the isolated compounds.
Reference: [1] Russian Journal of Organic Chemistry, 2018, vol. 54, # 3, p. 397 - 402[2] Zh. Org. Khim., 2018, vol. 54, # 3, p. 393 - 398,6
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